Poly[[(μ-1H-benzimidazole-5,6-dicarboxyl­ato)zinc(II)] monohydrate]

Li, Z.; Dai, J.; Yue, S.

doi:10.1107/S1600536809022107

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m775

doi:10.1107/S1600536809022107

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Poly[[(μ-1H-benzimidazole-5,6-dicarboxylato)zinc(II)] monohydrate]

Zhao-yang Li,^a Jing-wei Dai ^a and Shan-tang Yue ^a ^*

^aSchool of Chemistry and the Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: yuesht@scnu.edu.cn

(Received 17 May 2009; accepted 10 June 2009; online 13 June 2009)

The three-dimensional polymeric title compound, {[Zn(C₉H₄N₂O₄)]·H₂O}_n, contains one crystallographically independent Zn^II atom, one fully deprotonated 1H-benzimidazole-5,6-dicarboxylate (bdc) ligand and one uncoordinated water molecule. The Zn^II atom is four-coordinated by three O atoms and one N atom from the bdc ligands, giving a distorted tetrahedral coordination geometry. The uncoordinated water molecule is bound to the main structure through a strong bdc–water N—H⋯O hydrogen bond, and two much weaker water–bdc O—H⋯O interactions.

Related literature

For structures of other bdc complexes, see: Gao et al. (2008 ); Lo et al. (2007 ); Wei et al. (2008 ); Yao et al. (2008 ).

Experimental

Crystal data

[Zn(C₉H₄N₂O₄)]·H₂O
M_r = 287.55
Monoclinic, P 2₁ /c
a = 6.4735 (5) Å
b = 8.1836 (6) Å
c = 18.4407 (12) Å
β = 104.397 (2)°
V = 946.25 (12) Å³
Z = 4
Mo Kα radiation
μ = 2.61 mm⁻¹
T = 298 K
0.35 × 0.26 × 0.18 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.444, T_max = 0.625
4613 measured reflections
1665 independent reflections
1513 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.072
S = 1.06
1665 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1W	0.86	2.02	2.809 (3)	152
O1W—H1W⋯O1ⁱ	0.93	2.45	3.211 (5)	139
O1W—H2W⋯O4ⁱⁱ	0.91	2.29	3.095 (3)	146
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022107/bg2261sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022107/bg2261Isup2.hkl

checkCIF report

Comment top

N-Heterocyclic carboxylic acids have atracted attention not only because their versatile coordination modes but also owing to their forming high-dimensional polymers through H-bonding interactions. 1H-benzimidazole-5,6-dicarboxylic acid (bdc), having six coordination points, is a good candidate for the generation of three-dimensional coordination polymers. However, up to now the complexes based on the bdc ligand are rare (Lo et al., 2007; Gao et al., 2008; Wei et al., 2008; Yao et al., 2008). Here we report the first three-dimensional Zn coordination polymer connected by bdc ligands, [Zn(C₉H₄N₂O₂)].H₂O.

As is shown in Figure 1, the asymmetric unit consists of one Zn²⁺ cation, a fully deprotonated bdc^2- ligand, and a free water moelcule. The cation has a tetrahedral coordination environment, and is surrounded by three oxygen and one nitrogen atoms from the bdc ligands. A packing diagram showing the 3D structure coming out from the tetradentate character of the bdc ligand is shown in Figure 2. To the best of our knowledge, the title compound is the first 3D transition metal coordination polymer based on the 1H-benzimidazole-5,6-dicarboxylic acid ligand.

Related literature top

For some the structures of other bdc complexes, see: Gao et al. (2008); Lo et al. (2007); Wei et al. (2008); Yao et al. (2008).

Experimental top

A mixture of bdc (0.0415 g, 0.20 mmol), Zn(NO₃)₂.6H₂O (0.0594 g, 0.20 mmol) and water (10 ml) was heated up to 430 K for 72 h in a 23 ml Teflon-lined stainless-steel autoclave and then cooled down to room temperature in a 278 K/hour rate. Colourless prismatic crystals were collected and dried in air.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Displacement ellipsoid plot (50% probability level) of the title compound, with atom numbering. Symmetry codes: (i) -x, -y+2, -z+2; (ii) -x, y+1/2, -z+3/2; (iii) x-1, y, z.
	Fig. 2. The packing diagram of the title compound, with H atoms omitted for clarity. Hydrogen bonds are shown as dashed lines.

Poly[[(µ-1H-benzimidazole-5,6-dicarboxylato)zinc(II)] monohydrate] top

Crystal data top

[Zn(C₉H₄N₂O₄)]·H₂O	F(000) = 576
M_r = 287.55	D_x = 2.018 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2639 reflections
a = 6.4735 (5) Å	θ = 2.3–27.6°
b = 8.1836 (6) Å	µ = 2.61 mm⁻¹
c = 18.4407 (12) Å	T = 298 K
β = 104.397 (2)°	Block, colorless
V = 946.25 (12) Å³	0.35 × 0.26 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	1665 independent reflections
Radiation source: fine-focus sealed tube	1513 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −7→7
T_min = 0.444, T_max = 0.625	k = −9→8
4613 measured reflections	l = −21→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0407P)² + 0.8076P] where P = (F_o² + 2F_c²)/3
1665 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Zn(C₉H₄N₂O₄)]·H₂O	V = 946.25 (12) Å³
M_r = 287.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.4735 (5) Å	µ = 2.61 mm⁻¹
b = 8.1836 (6) Å	T = 298 K
c = 18.4407 (12) Å	0.35 × 0.26 × 0.18 mm
β = 104.397 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	1665 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1513 reflections with I > 2σ(I)
T_min = 0.444, T_max = 0.625	R_int = 0.019
4613 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.06	Δρ_max = 0.54 e Å⁻³
1665 reflections	Δρ_min = −0.32 e Å⁻³
154 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6805 (4)	0.7618 (3)	1.14674 (15)	0.0244 (6)
H1	0.7562	0.7565	1.1967	0.029*
C2	0.4362 (4)	0.8133 (3)	1.04587 (14)	0.0210 (6)
C3	0.5993 (4)	0.7274 (3)	1.02485 (14)	0.0209 (6)
C4	0.5896 (4)	0.6922 (3)	0.95017 (14)	0.0232 (6)
H4	0.6986	0.6358	0.9364	0.028*
C5	0.2433 (4)	0.8286 (3)	0.91858 (14)	0.0210 (6)
C6	0.2567 (4)	0.8630 (3)	0.99290 (14)	0.0225 (6)
H6	0.1474	0.9184	1.0070	0.027*
C7	0.4108 (4)	0.7447 (3)	0.89738 (14)	0.0198 (5)
C8	0.0478 (4)	0.8790 (3)	0.85989 (15)	0.0244 (6)
C9	0.4056 (4)	0.7163 (3)	0.81632 (14)	0.0200 (6)
N1	0.4937 (3)	0.8337 (3)	1.12397 (12)	0.0223 (5)
N2	0.7500 (3)	0.6973 (3)	1.09061 (12)	0.0255 (5)
H2	0.8682	0.6459	1.0948	0.031*
O1	0.0221 (4)	0.8307 (4)	0.79625 (13)	0.0700 (10)
O2	−0.0815 (3)	0.9719 (3)	0.88154 (11)	0.0371 (5)
O3	0.3461 (3)	0.5800 (3)	0.78853 (10)	0.0317 (5)
O4	0.4720 (4)	0.8254 (3)	0.78041 (11)	0.0360 (5)
Zn1	−0.35253 (5)	1.02462 (4)	0.814219 (16)	0.02108 (13)
O1W	1.1216 (4)	0.5187 (3)	1.15400 (15)	0.0533 (7)
H1W	1.0604	0.4556	1.1853	0.080*
H2W	1.1968	0.6024	1.1810	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0238 (14)	0.0330 (16)	0.0141 (13)	0.0009 (12)	0.0004 (11)	0.0029 (11)
C2	0.0226 (13)	0.0263 (14)	0.0138 (13)	0.0008 (11)	0.0037 (11)	−0.0001 (10)
C3	0.0189 (13)	0.0270 (15)	0.0153 (13)	0.0023 (11)	0.0013 (11)	0.0010 (11)
C4	0.0215 (13)	0.0306 (15)	0.0177 (14)	0.0056 (11)	0.0053 (11)	−0.0025 (11)
C5	0.0212 (13)	0.0264 (15)	0.0146 (13)	0.0006 (11)	0.0029 (11)	−0.0019 (10)
C6	0.0206 (13)	0.0310 (15)	0.0159 (13)	0.0052 (11)	0.0046 (11)	−0.0016 (11)
C7	0.0222 (13)	0.0220 (14)	0.0151 (13)	−0.0006 (11)	0.0043 (10)	−0.0015 (10)
C8	0.0230 (14)	0.0329 (16)	0.0160 (14)	0.0016 (12)	0.0025 (11)	−0.0013 (11)
C9	0.0174 (12)	0.0266 (15)	0.0152 (12)	0.0018 (10)	0.0025 (10)	−0.0009 (11)
N1	0.0239 (12)	0.0313 (13)	0.0107 (11)	0.0047 (10)	0.0026 (9)	0.0001 (9)
N2	0.0208 (12)	0.0352 (14)	0.0189 (12)	0.0083 (10)	0.0017 (9)	0.0002 (10)
O1	0.0496 (15)	0.125 (3)	0.0230 (13)	0.0460 (16)	−0.0143 (11)	−0.0294 (14)
O2	0.0285 (11)	0.0578 (15)	0.0209 (11)	0.0200 (10)	−0.0012 (9)	−0.0072 (9)
O3	0.0511 (13)	0.0269 (11)	0.0190 (10)	−0.0077 (10)	0.0125 (9)	−0.0057 (8)
O4	0.0532 (14)	0.0376 (13)	0.0185 (10)	−0.0200 (10)	0.0117 (10)	−0.0050 (9)
Zn1	0.0221 (2)	0.0270 (2)	0.01325 (19)	0.00140 (12)	0.00268 (13)	−0.00017 (12)
O1W	0.0410 (14)	0.0652 (18)	0.0468 (16)	0.0148 (12)	−0.0022 (12)	−0.0085 (12)

Geometric parameters (Å, º) top

C1—N1	1.316 (3)	C6—H6	0.9300
C1—N2	1.336 (3)	C7—C9	1.505 (4)
C1—H1	0.9300	C8—O1	1.210 (3)
C2—C6	1.380 (4)	C8—O2	1.266 (3)
C2—C3	1.401 (4)	C9—O3	1.247 (3)
C2—N1	1.405 (3)	C9—O4	1.250 (3)
C3—N2	1.376 (3)	N2—H2	0.8600
C3—C4	1.393 (4)	Zn1—O2	1.929 (2)
C4—C7	1.383 (4)	Zn1—N1ⁱ	1.999 (2)
C4—H4	0.9300	Zn1—O3ⁱⁱ	1.9587 (19)
C5—C6	1.381 (4)	Zn1—O4ⁱⁱⁱ	1.996 (2)
C5—C7	1.418 (4)	O1W—H1W	0.9333
C5—C8	1.504 (4)	O1W—H2W	0.9127

N1—C1—N2	112.9 (2)	O1—C8—C5	119.8 (3)
N1—C1—H1	123.6	O2—C8—C5	116.2 (2)
N2—C1—H1	123.6	O3—C9—O4	122.2 (2)
C6—C2—C3	120.8 (2)	O3—C9—C7	118.3 (2)
C6—C2—N1	130.8 (2)	O4—C9—C7	119.3 (2)
C3—C2—N1	108.5 (2)	C1—N1—C2	105.2 (2)
N2—C3—C4	133.0 (2)	C1—N1—Zn1ⁱ	126.26 (18)
N2—C3—C2	105.3 (2)	C2—N1—Zn1ⁱ	127.64 (17)
C4—C3—C2	121.7 (2)	C1—N2—C3	108.1 (2)
C7—C4—C3	117.1 (2)	C1—N2—H2	125.9
C7—C4—H4	121.4	C3—N2—H2	125.9
C3—C4—H4	121.4	C8—O2—Zn1	119.85 (18)
C6—C5—C7	120.6 (2)	C9—O3—Zn1^iv	121.73 (18)
C6—C5—C8	119.5 (2)	C9—O4—Zn1^v	131.46 (18)
C7—C5—C8	119.9 (2)	O2—Zn1—O3ⁱⁱ	116.08 (9)
C2—C6—C5	118.5 (2)	O2—Zn1—O4ⁱⁱⁱ	111.99 (10)
C2—C6—H6	120.8	O3ⁱⁱ—Zn1—O4ⁱⁱⁱ	91.96 (9)
C5—C6—H6	120.8	O2—Zn1—N1ⁱ	103.56 (9)
C4—C7—C5	121.3 (2)	O3ⁱⁱ—Zn1—N1ⁱ	122.67 (9)
C4—C7—C9	117.4 (2)	O4ⁱⁱⁱ—Zn1—N1ⁱ	110.27 (9)
C5—C7—C9	121.3 (2)	H1W—O1W—H2W	109.2
O1—C8—O2	124.0 (3)

C6—C2—C3—N2	−179.7 (3)	C5—C7—C9—O3	−99.2 (3)
N1—C2—C3—N2	0.4 (3)	C4—C7—C9—O4	−92.4 (3)
C6—C2—C3—C4	1.5 (4)	C5—C7—C9—O4	84.8 (3)
N1—C2—C3—C4	−178.4 (3)	N2—C1—N1—C2	0.3 (3)
N2—C3—C4—C7	−178.8 (3)	N2—C1—N1—Zn1ⁱ	−169.63 (19)
C2—C3—C4—C7	−0.5 (4)	C6—C2—N1—C1	179.7 (3)
C3—C2—C6—C5	−1.1 (4)	C3—C2—N1—C1	−0.4 (3)
N1—C2—C6—C5	178.8 (3)	C6—C2—N1—Zn1ⁱ	−10.6 (4)
C7—C5—C6—C2	−0.2 (4)	C3—C2—N1—Zn1ⁱ	169.32 (18)
C8—C5—C6—C2	179.0 (3)	N1—C1—N2—C3	0.0 (3)
C3—C4—C7—C5	−0.9 (4)	C4—C3—N2—C1	178.4 (3)
C3—C4—C7—C9	176.3 (2)	C2—C3—N2—C1	−0.2 (3)
C6—C5—C7—C4	1.3 (4)	O1—C8—O2—Zn1	7.0 (5)
C8—C5—C7—C4	−178.0 (3)	C5—C8—O2—Zn1	−173.02 (19)
C6—C5—C7—C9	−175.8 (3)	O4—C9—O3—Zn1^iv	0.2 (4)
C8—C5—C7—C9	4.9 (4)	C7—C9—O3—Zn1^iv	−175.59 (17)
C6—C5—C8—O1	−170.2 (3)	O3—C9—O4—Zn1^v	−160.8 (2)
C7—C5—C8—O1	9.1 (5)	C7—C9—O4—Zn1^v	14.9 (4)
C6—C5—C8—O2	9.8 (4)	C8—O2—Zn1—O3ⁱⁱ	−44.1 (3)
C7—C5—C8—O2	−170.9 (3)	C8—O2—Zn1—O4ⁱⁱⁱ	59.7 (2)
C4—C7—C9—O3	83.6 (3)	C8—O2—Zn1—N1ⁱ	178.5 (2)

Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x, y+1/2, −z+3/2; (iii) x−1, y, z; (iv) −x, y−1/2, −z+3/2; (v) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1W	0.86	2.02	2.809 (3)	152
O1W—H1W···O1^vi	0.93	2.45	3.211 (5)	139
O1W—H2W···O4^vii	0.91	2.29	3.095 (3)	146

Symmetry codes: (vi) −x+1, −y+1, −z+2; (vii) x+1, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₉H₄N₂O₄)]·H₂O
M_r	287.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	6.4735 (5), 8.1836 (6), 18.4407 (12)
β (°)	104.397 (2)
V (Å³)	946.25 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.61
Crystal size (mm)	0.35 × 0.26 × 0.18

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.444, 0.625
No. of measured, independent and observed [I > 2σ(I)] reflections	4613, 1665, 1513
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.072, 1.06
No. of reflections	1665
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.32

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1W	0.86	2.02	2.809 (3)	152.4
O1W—H1W···O1ⁱ	0.93	2.45	3.211 (5)	139.2
O1W—H2W···O4ⁱⁱ	0.91	2.29	3.095 (3)	146.3

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, −y+3/2, z+1/2.

Acknowledgements

This work was supported financially by the Nature and Science Foundation of Guangdong Province (grant No. 7005808), Guangdong Provincial Science and Technology Bureau (grant 2008B010600009) and the NSFC (grant No. U0734005).

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gao, Q., Gao, W.-H., Zhang, C.-Y. & Xie, Y.-B. (2008). Acta Cryst. E64, m928. Web of Science CrossRef IUCr Journals Google Scholar
Lo, Y.-L., Wang, W.-C., Lee, G.-A. & Liu, Y.-H. (2007). Acta Cryst. E63, m2657–m2658. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wei, Y.-Q., Yu, Y.-F. & Wu, K.-C. (2008). Cryst. Growth Des. 8, 2087–2089. Web of Science CrossRef CAS Google Scholar
Yao, Y.-L., Che, Y.-X. & Zheng, J.-M. (2008). Cryst. Growth Des. 8, 2299–2306. Web of Science CSD CrossRef CAS Google Scholar